Herbicidal sulfonamides

ABSTRACT

The invention relates to certain sulfonylurea compounds having a carbocyclic or heterocyclic ring ortho to the sulfonylurea linkage, compositions thereof and a method of their use as herbicides or plant growth regulants.

BACKGROUND OF THE INVENTION

The invention relates to certain sulfonylurea compounds having acarbocyclic or heterocyclic ring linked indirectly ortho to thesulfonylurea linkage, compositions thereof and a method of their use asherbicides or plant growth regulants.

New compounds effective for controlling the growth of undesiredvegetation are in constant demand. In the most common situation, suchcompounds are sought to selectively control the growth of weeds inuseful crops such as cotton, rice, corn, wheat and soybeans, to name afew. Unchecked weed growth in such crops can cause significant losses,reducing profit to the farmer and increasing costs to the consumer. Inother situations, herbicides are desired which will control all plantgrowth. Examples of areas in which complete control of all vegetation isdesired are areas around fuel storage tanks, ammunition depots andindustrial storage areas. There are many products commercially availablefor these purposes, but the search continues for products which are moreeffective, less costly and environmentally safe.

U.S. Pat. Nos. 4,127,405 and 4,169,719 disclose herbicidalbenzenesulfonylureas.

European Patent Application (EP-A) No. 83,975, published July 20, 1983,discloses herbicidal benzenesulfonamides of formula ##STR1## wherein Qis selected from various five or six-membered aromatic or particallyunsaturated heterocyclic rings containing 2 or 3 heteroatoms selectedfrom O, S or NR.

European Patent Application (EP-A) No. 85,476, published Aug. 10, 1983,discloses herbicidal benzenesulfonamides of formulae ##STR2## wherein Qis selected from various 5-membered aromatic heterocycles, and theirdihydro and tetrahydro analogs, which contain one heteroatom selectedfrom O, S or NR, or Q is a saturated or partially unsaturated 6-memberedring containing one heteroatom selected from O or S; and

Q¹ is a 6-membered aromatic heterocycle contaning one to three N atoms.

South African Patent Application No. 83/8416, published May 12, 1984,discloses herbicidal benzenesulfonamides of formula ##STR3## wherein Ais an unsaturated or only partially saturated 5- or 6-memberedheterocyclic ring system which is bonded through a carbon atom andcontains 1, 2 or 3 heteroatoms.

European Patent Application No. 116,518, published Aug. 22, 1984,discloses herbicidal sulfonamides of formula ##STR4## wherein X is##STR5## A is CO, SO₂, CONR₂₃ or CO₂ ; B is C₁ -C₄ alkyl or C₂ -C₄alkenyl; and

C is CO, CR₂₁ R₂₂ or SO₂.

U.S. Pat. No. 4,475,944 discloses herbicidal sulfamates, possessing anortho-heterocyclic ring, such as those of formula ##STR6## wherein W isO, S or NR₁.

European Patent Application (EP-A) No. 141,777 (Swiss priority 9/9/83,published 6/15/85) discloses herbicidal sulfonamides of formula ##STR7##wherein R³ is H, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or CN;

R⁴ is H or C₁ -C₄ alkyl;

A is ##STR8## R¹⁷ is a 5- to 6-membered heterocyclic radical; Y is O, Sor a direct bond; and n is 0 or 1.

South African Patent Application No. 83/0441 (Swiss priority 1/25/82)discloses herbicidal benzenesulfonamides of formula ##STR9## wherein R₁is H, halogen, NO₂, C₁ -C₄ haloalkyl, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₂-C₅ alkenyl or C₁ -C₄ alkoxycarbonyl;

R₂ is C₁ -C₃ alkyl or C₁ -C₃ alkoxy, each unsubstituted or substitutedby 1 to 3 halogen atoms;

R₃ is halogen, H, NR₄ R₅, C₁ -C₃ alkyl, unsubstituted or substituted by1 to 3 halogen atoms or C₁ -C₄ alkoxy, or is C₁ -C₃ alkoxy,unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogenatoms;

A is C₁ -C₄ alkylene or C₂ -C₄ alkenylene, each unsubstituted orsubstituted by C₁ -C₄ alkyl;

m is 0 or 1;

E is N or CH;

X is oxygen, sulfur, SO or SO₂ ; and

Q is, in part, a 5- or 6-membered heterocyclic ring or a fused homologuethereof, each linked through a carbon atom to the bridge --X--A_(m) --or, if the heterocyclic ring contains nitrogen, is also bound through anitrogen atom, and which is unsbustituted or mono- to trisubstituted byhalogen, cyano, nitro, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ 14 C₄ alkylthio,C₂ -C₅ alkenyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxycarbonyl, --NR₁₅ R₁₆ or--SO--NR₁₇ R₁₈.

SUMMARY OF THE INVENTION

Now new herbicidal compounds and compositions thereof have been foundthat function as preemergent or postemergent herbicides or as plantgrowth regulants. The compounds of the invention are compounds ofFormula I ##STR10## W is O or S; R is H or CH₃ ;

E₁ is O, S, SO, SO₂ or a single bond;

X_(a) is CH₂, CH(CH₃), CH₂ CH₂, CH₂ CH₂ CH₂ or CO;

E is a single bond, CH₂ or O;

Q is a 5- or 6-membered carbocyclic ring containing either one or twocarbonyl groups and 0-1 endocyclic double bonds; a 5-memberedheterocyclic ring, containing 2-4 atoms of carbon and 1-3 heteroatomsselected from the group consisting of 0-2 oxygen, 0-2 sulfur or 0-3nitrogen, wherein sulfur may take the form of S, SO or SO₂, andcontaining one or two carbonyl or sulfonyl (SO₂) groups, or one carbonyland one sulfonyl group and 0-1 endocyclic double bonds; or a 6-memberedheterocyclic ring, containing 2-5 atoms of carbon and 1-3 heteroatomsselected from the group consisting of 0-2 oxygen, 0-2 sulfur or 0-3nitrogen, wherein sulfur may take the form of S, SO or SO₂, andcontaining one or two carbonyl or sulfonyl (SO₂) groups, or one carbonyland one sulfonyl group and 0-2 endocyclic double bonds; said Q value mayfurther be optionally substituted with 1-2 substituent groups:substituents on carbon may be selected from the group consisting ofhalogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, CH₂ (C₂ -C₃ alkenyl), CH₂ (C₂-C₃ alkynyl), C₂ -C₄ alkoxycarbonyl, CN, OH, C₁ -C₃ alkoxy, C₁ -C₃alkylthio, C₁ -C₃ alkylsulfinyl, C₁ -C.sub. 3 alkylsulfonyl or C₂ -C₄alkylcarbonyl; substitutents on nitrogen may be selected from the groupconsisting of C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, CH₂ (C₂ -C₃ alkenyl), CH₂(C₂ -C₃ alkynyl), C₂ -C₄ alkoxycarbonyl or C₂ -C₄ alkylcarbonyl;

R₁ is H, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, halogen, nitro, C₁ -C₃ alkoxy,SO₂ NR_(a) R_(b), C₁ -C₃ alkylthio, C₁ -C₃ alkylsulfinyl, C₁ -C₃alkylsulfonyl, CH₂ CN, CN, CO₂ R_(c), C₁ -C₃ haloalkoxy, C₁ -C₃haloalkylthio, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkylthioalkyl, CH₂ N₃ orNR_(d) R_(e) ;

R_(a) is H, C₁ -C₄ alkyl, C₂ -C₃ cyanoalkyl, methoxy or ethoxy;

R_(b) is H, C₁ -C₄ alkyl or C₃ -C₄ alkenyl; or

R_(a) and R_(b) may be taken together as --(CH₂)₃ --, --(CH₂)₄ --,--(CH₂)₅ -- or --CH₂ CH₂ OCH₂ CH₂ --;

R_(c) is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₂ -C₄ haloalkyl,C₂ -C₃ cyanoalkyl, C₅ -C₆ cycloalkyl, C₄ -C₇ cycloalkylalkyl or C₂ -C₄alkoxyalkyl;

R_(d) and R_(e) are independently H or C₁ -C₂ alkyl; ##STR11## X is H,C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkyl, C₁ -C₄haloalkylthio, C₁ -C₄ alkylthio, halogen, C₂ -C₅ alkoxyalkyl, C₂ -C₅alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃ alkyl)amino or C₃ -C₅cycloalkyl;

Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄haloalkylthio, C₁ -C₄ alkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃ alkyl)amino, C₃ -C₄alkenyloxy, C₃ -C₄ alkynyloxy, C₂ -C₅ alkylthioalkyl, C₁ -C₄ haloalkyl,C₂ -C₄ alkynyl, azido, cyano, C₂ -C₅ alkylsulfinylalkyl, C₂ -C₅alkylsulfonylalkyl, ##STR12## m is 2 or 3; L₁ and L₂ are independently Oor S;

R₂ is H or C₁ -C₃ alkyl;

R₃ and R₄ are independently C₁ -C₃ alkyl;

Z is CH, N, CCH₃, CC₂ H₅, CCl or CBr;

Z₁ is CH or N;

Y₁ is O or CH₂ ;

X₁ is CH₃, OCH₃, OC₂ H₅ or OCF₂ H;

X₂ is CH₃, C₂ H₅ or CH₂ CF₃ ;

Y₂ is OCH₃, OC₂ H₅, SCH₃, SC₂ H₅, CH₃ or CH₂ CH₃ ;

X₃ is CH₃ or OCH₃ ;

Y₃ is H or CH₃ ;

X₄ is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃ or Cl; and

Y₄ is CH₃, OCH₃, OC₂ H₅ or Cl;

and their agriculturally suitable salts; provided that

(a) when Q contains 2 heteroatoms selected from 0-2 oxyen and 0-2sulfur, said heteroatoms are not bonded directly to one another unlessin the form O--SO₂, and when Q contains 3 nitrogen heteroatoms, only twoof these may be bonded directly together;

(b) when X is Cl, F, Br or I, then Z is CH and Y is OCH₃, OC₂ H₅,N(OCH₃)CH₃, NHCH₃, N(CH₃)₂ or OCF₂ H;

(c) when X or Y is C₁ haloalkoxy, then Z is CH;

(d) when J is J-2 or J-3, the substituent E₁ X_(a) Q and thesulfonylurea bridge are on adjacent carbon atoms;

(e) when E is O, then J is J-1 and W is O;

(f) when W is S, then R is H, A is A-1, Z is CH or N and Y is CH₃, OCH₃,OC₂ H₅, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂OCH₃, CH(OCH₃)₂ or 1,3-dioxolan-2-yl;

(g) when the total number of carbon atoms of X and Y is greater thanfour, then the number of carbons of R₁ must be less than or equal totwo, and the number of carbons of the substituent on Q must also be lessthan or equal to two;

(h) X₄ and Y₄ are not simultaneously Cl;

(i) when A is A-1 J is J-1 wherein E is a single bond, X_(a) is CH₂,CH(CH₃) or CH₂ CH₂ and Q is a 5-membered heterocyclic ring containingone endocyclic double bond or a 6-membered heterocyclic ring containing1 or 2 endocyclic double bonds which is unsubstituted or substituted byone or more C₁ -C₄ alkyl groups then said heterocycle must contain atleast one nitrogen and be bound to X_(a) through nitrogen; and

(j) when X_(a) is CO, then E₁ is a single bond.

Representative examples of preferred Q include: ##STR13## wherein Q-1through Q-87 may be optionally substituted with 1 or 2 groups selectedfrom C₁ -C₂ alkyl or C₁ -C₂ haloalkyl;

R₅ and R₆ are independently H or C₁ -C₃ alkyl;

X_(b) is O or NR₅ ; and

X_(c) is O, S, SO, SO₂ or NR₅.

In the above definitions, the term "alkyl", used either alone or incompound words such as "alkylthio" or "haloalkyl", denotes straightchain or branched alkyl, e.g. methyl, ethyl, n-propyl, isopropyl or thedifferent butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropyloxy and thedifferent butyl isomers.

Alkenyl denotes straight chain or branched alkenes, e.g. vinyl,1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.

Alkynyl denotes straight chain or branch alkynes, e.g., ethynyl,1-propynyl, 2-propynyl and the different butynyl isomers.

Alkylsulfonyl denotes methylsulfonyl, ethylsulfonyl and the differentpropylsulfonyl isomers.

Alkylthio, alkylsulfinyl, alkylamino, alkylsulfamoyl, etc. are definedin an analogous manner.

Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term "halogen", either alone or in compound words such as"haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as "haloalkyl" said alkyl may bepartially halogenated or fully substituted with halogen atoms which maybe the same or different. Examples of haloalkyl include CH₂ CH₂ F, CF₂CF₃ and CH₂ CHFCl.

Alkylcarbonyl denotes acetyl, propionyl, and the different butyrylisomers.

Alkoxycarbonyl denotes methoxycarbonyl, ethoxycarbonyl, propoxycarbonyland isopropoxycarbonyl.

The total number of carbon atoms in a substituent group is indicated bythe C_(i) -C_(j) prefix where i and j are numbers from 1 to 10. Forexample, C₂ cyanoalkyl would designate CH₂ CN, C₃ cyanoalkyl woulddesignate CH₂ CH₂ CN and CH(CN)CH₃, and C₂ -C₃ alkylthioalkyl woulddesignate CH₂ SCH₃, CH₂ SC₂ H₅, CH₂ CH₂ SCH₃ or CH(CH₃)SCH₃, and C₂ -C₅alkoxyalkoxy would represent OCH₂ OCH₃ through O(CH₂)₄ OCH₃ or OCH₂O(CH₂)₃ CH₃ and the various structural isomers embraced therein.

Preferred for reasons of increased ease of synthesis and/or greaterherbicidal efficacy are:

1. Compounds of Formula I where E is a single bond and Z is CH or N;

2. Compounds of Formula I where E is CH₂, W is O, Z is CH or N and E₁ isa single bond;

3. Compounds of Formula I where E is O, Z is CH or N and E₁ is a singlebond.

4. Compounds of Preferred 1 where Q is Q-1 to Q-87;

wherein

Q-1 through Q-87 may be optionally substituted with 1 or 2 groupsselected from C₁ -C₂ alkyl or C₁ -C₂ haloalkyl;

R₅ and R₆ are independently H or C₁ -C₃ alkyl;

X_(b) is O or NR₅ ; and

X_(c) is O, S, SO, SO₂ or NR₅.

5. Compounds of Preferred 4 where

W is O;

E₁ is a single bond;

X_(a) is CH₂ or CH₂ CH₂ ;

R is H;

R₁ is H, F, Cl, Br, C₁ -C₂ alkyl, C₁ -C₃ alkoxy, C₁ -C₃ alkylthio, or C₁-C₂ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio substituted with 1-3 atomsof F, Cl or Br;

X is C₁ -C₂ alkyl, C₁ -C₂ alkoxy, Cl, F, Br, I, OCF₂ H, CH₂ F, CF₃, OCH₂CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br; and

Y is H, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, ##STR14## cyclopropyl, C.tbd.CH orC.tbd.CCH₃ ; 6. Compounds of Preferred 5 where A is A-1;

7. Compounds of Preferred 6 where J is J-1;

8. Compounds of Preferred 6 where J is J-2;

9. Compounds of Preferred 6 where J is J-3;

10. Compounds of Preferred 6 where J is J-4;

11. Compounds of Preferred 6 where J is J-5;

12. Compounds of Preferred 6 where

J is J-1;

R₁ is H, Cl, CH₃ or OCH₃ ;

X is CH₃, OCH₃, Cl or OCF₂ H; and

Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃, CH(OCH₃)₂ or cyclopropyl;

13. Compounds of Preferred 12 where Q is Q-1;

14. Compounds of Preferred 12 where Q is Q-2;

15. Compounds of Preferred 12 where Q is Q-3;

16. Compounds of Preferred 12 where Q is Q-4;

17. Compounds of Preferred 12 where Q is Q-5;

18. Compounds of Preferred 12 where Q is Q-6;

19. Compounds of Preferred 12 where Q is Q-7;

20. Compounds of Preferred 12 where Q is Q-8;

21. Compounds of Preferred 12 where Q is Q-9;

22. Compounds of Preferred 12 where Q is Q-10;

23. Compounds of Preferred 12 where Q is Q-11;

24. Compounds of Preferred 12 where Q is Q-12;

25. Compounds of Preferred 12 where Q is Q-13;

26. Compounds of Preferred 12 where Q is Q-14;

27. Compounds of Preferred 12 where Q is Q-15;

28. Compounds of Preferred 12 where Q is Q-16;

29. Compounds of Preferred 12 where Q is Q-17;

30. Compounds of Preferred 12 where Q is Q-18;

31. Compounds of Preferred 12 where Q is Q-19;

32. Compounds of Preferred 12 where Q is Q-20;

33. Compounds of Preferred 12 where Q is Q-21;

34. Compounds of Preferred 12 where Q is Q-22;

35. Compounds of Preferred 12 where Q is Q-23;

36. Compounds of Preferred 12 where Q is Q-24;

37. Compounds of Preferred 12 where Q is Q-25;

38. Compounds of Preferred 12 where Q is Q-26;

39. Compounds of Preferred 12 where Q is Q-27;

40. Compounds of Preferred 12 where Q is Q-28;

41. Compounds of Preferred 12 where Q is Q-29;

42. Compounds of Preferred 12 where Q is Q-30;

43. Compounds of Preferred 12 where Q is Q-31;

44. Compounds of Preferred 12 where Q is Q-32;

45. Compounds of Preferred 12 where Q is Q-33;

46. Compounds of Preferred 12 where Q is Q-34;

47. Compounds of Preferred 12 where Q is Q-35;

48. Compounds of Preferred 12 where Q is Q-36;

49. Compounds of Preferred 12 where Q is Q-37;

50. Compounds of Preferred 12 where Q is Q-38;

51. Compounds of Preferred 12 where Q is Q-39;

52. Compounds of Preferred 12 where Q is Q-40;

53. Compounds of Preferred 12 where q is Q-41;

54. Compounds of Preferred 12 where Q is Q-42;

55. Compounds of Preferred 12 where Q is Q-43;

56. Compounds of Preferred 12 where Q is Q-44;

57. Compounds of Preferred 12 where Q is Q-45;

58. Compounds of Preferred 12 where Q is Q-46;

59. Compounds of Preferred 12 where Q is Q-47;

60. Compounds of Preferred 12 where Q is Q-48;

61. Compounds of Preferred 12 where Q is Q-49;

62. Compounds of Preferred 12 where Q is Q-50;

63. Compounds of Preferred 12 where Q is Q-51;

64. Compounds of Preferred 12 where Q is Q-52;

65. Compounds of Preferred 12 where Q is Q-53;

66. Compounds of Preferred 12 where Q is Q-54;

67. Compounds of Preferred 12 where Q is Q-55;

68. Compounds of Preferred 12 where Q is Q-56;

69. Compounds of Preferred 12 where Q is Q-57;

70. Compounds of Preferred 12 where Q is Q-58;

71. Compounds of Preferred 12 where Q is Q-59;

72. Compounds of Preferred 12 where Q is Q-60;

73. Compounds of Preferred 12 where Q is Q-61;

74. Compounds of Preferred 12 where Q is Q-62;

75. Compounds of Preferred 12 where Q is Q-63;

76. Compounds of Preferred 12 where Q is Q-64;

77. Compounds of Preferred 12 where Q is Q-65;

78. Compounds of Preferred 12 where Q is Q-66;

79. Compounds of Preferred 12 where Q is Q-67;

80. Compounds of Preferred 12 where Q is Q-68;

81. Compounds of Preferred 12 where Q is Q-69;

82. Compounds of Preferred 12 where Q is Q-70;

83. Compounds of Preferred 12 where Q is Q-71;

84. Compounds of Preferred 12 where Q is Q-72;

85. Compounds of Preferred 12 where Q is Q-73;

86. Compounds of Preferred 12 where Q is Q-74;

87. Compounds of Preferred 12 where Q is Q-75;

88. Compounds of Preferred 12 where Q is Q-76;

89. Compounds of Preferred 12 where Q is Q-77;

90. Compounds of Preferred 12 where Q is Q-78;

91. Compounds of Preferred 12 where Q is Q-79;

92. Compounds of Preferred 12 where Q is Q-80;

93. Compounds of Preferred 12 where Q is Q-81;

94. Compounds of Preferred 12 where Q is Q-82;

95. Compounds of Preferred 12 where Q is Q-83;

96. Compounds of Preferred 12 where Q is Q-84;

97. Compounds of Preferred 12 where Q is Q-85;

98. Compounds of Preferred 12 where Q is Q-86;

99. Compounds of Preferred 12 where Q is Q-87;

100. Compounds of Preferred 2 where

R is H;

J is J-1;

R₁ is H;

A is A-1;

X is CH₃, OCH₃, OCH₂ CH₃, Cl or OCF₂ H;

Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃, CH(OCH₃)₂ or cyclopropyl; Z isCH or N; and Q is Q-1, Q-4, Q-5, Q-7, Q-10, Q-11, Q-12, Q-17, Q-19,Q-20, Q-24, Q-25, Q-27, Q-28, Q-36, Q-38, Q-46, Q-47, Q-54, Q-56, Q-59,W-60, Q-63, Q-71, Q-74, Q-76, Q-78 and Q-79;

101. Compounds of Preferred 3 where

R is H;

R₁ is H;

A is A-1;

X is CH₃, OCH₃, OCH₂ CH₃, Cl or OCF₂ H;

Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃, CH(OCH₃)₂ or cyclopropyl; Z isCH or N; and Q is Q-1, Q-4, Q-5, Q-7, Q-10, Q-11, Q-12, Q-17, Q-19,Q-20, Q-24, Q-25, Q-27, Q-28, Q-36, Q-38, Q-46, Q-47, Q-54, Q-56, Q-59,Q-60, Q-63, Q-71, Q-74, Q-76, Q-78 and Q-79.

102. Compounds of Formula I wherein

E₁ is a single bond.

X_(a) is CH₂, CH(CH₃), CH₂ CH₂ or CH₂ CH₂ CH₂ ;

Q is a saturated or partially saturated 5- or 6-membered carbocyclicring, containing either one or two carbonyl groups, or a saturated orpartially saturated 5- or 6-membered heterocyclic ring, containing 2-5atoms of carbon and 1-3 heteroatoms selected from the group consistingof 0-2 oxygen, 0-2 sulfur or 0-3 nitrogen, wherein sulfur may take theform of S, SO or SO₂, and containing one or two carbonyl or sulfonyl(SO₂) groups, or one carbonyl and one sulfonyl group; Q may further beoptionally substituted with 1-2 substituent groups: substituents oncarbon may be selected from the group consisting of halogen, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, CH₂ (C₂ -C₃ alkenyl), CH₂ (C₂ -C₃ alkynyl), C₂-C₄ alkoxycarbonyl, CN, OH, C₁ -C₃ alkoxy, C₁ -C₃ alkylthio, C₁ -C₃ C₁-C₃ alkylsulfinyl, C₁ -C₃ alkylsulfonyl or C₂ -C₄ alkylcarbonyl,substituents on nitrogen may be selected from the group consisting of C₁-C₄ alkyl, C₁ -C₄ haloalkyl, CH₂ (C₂ -C₃ alkenyl), CH₂ (C.sub. 2 -C₃alkynyl), C₂ -C₄ alkoxycarbonyl or C₂ -C₄ alkylcarbonyl;

R₁ is H, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, halogen, nitro, C₁ -C₃ alkoxy,SO₂ NR_(a) R_(b), C₁ -C₃ alkylthio, C₁ -C₃ alkylsulfinyl, C₁ -C₃alkylsulfonyl, CH₂ CN, CN, CO₂ R_(c), C₁ -C₃ haloalkoxy or C₁ -C₃haloalkylthio; ##STR15##

Specifically Preferred for reasons of greatest ease of synthesis and/orgreatest herbicidal efficacy are:

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-oxo-1-pyrrolidinylmethyl)benzenesulfonamide,m.p. 185°-187° C.;

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-oxo-1-pyrrolidinylmethyl)benzenesulfonamide,m.p. 194°-195° C.;

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-oxo-3-oxazolidinylmethyl)-3-thiophenesulfonamide,m.p. 157°-160° C.; and

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-oxo-3-oxazolidinylmethyl)-3-thiophenesulfoamide,m.p. 155°-161° C.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

Compounds of Formula I, wherein E is CH₂ or a single bond, can besynthesized by one or more of the procedures outlined in Equation 1.##STR16## wherein J, R, and A are as previously defined, provided E isCH₂ or a single bond.

The reaction of Equation 1a can be carried out according to proceduresdescribed in U.S. Pat. No. 4,127,405.

The sulfonyl isocyanates II are prepared from the correspondingsulfonamides of Formula IV according to procedures described in UnitedStates Pat. No. 4,238,621 or by the procedure of H. Ulrich, B. Tucker,and A. Sayigh, J. Org. Chem., 34, 3200 (1969).

Sulfonyl isothiocyanates (II, W is S) are known in the art and areprepared from the corresponding sulfonamides (IV) by reaction withcarbon disulfide and potassium hydroxide followed by treatment of theresulting dipotassium salt VI phosgene. Such a procedure is described inArch. Pharm. 299, 174 (1966).

Alternatively compounds of Formula I can be prepared according toEquation 1b or by the reaction of Equation 1c as described in U.S. Pat.No. 4,443,243.

The sulfonylureas of Formula I, wherein E is O, can be prepared by oneor both of the procedures described in Equation 2. ##STR17## wherein Jis as previously defined, provided E is O.

Phenols of Formula VII react with chlorsulfonylisocyanate (CSI) underelevated temperatures (Equation 2a) to provide the sulfonyl isocyanatesII, which react with heterocyclic amines of Formula III to yield thesulfonylureas I according to the procedure in U.S. Pat. No. 4,475,944.Alternatively, the reaction of Equation 2b may be employed according tothe procedure described in U.S. Pat. No. 4,391,976.

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by contacting compounds of Formula Iwith a solution of an alkali or alkaline earth metal salt having asufficiently basic anion (e.g., hydroxide, alkoxide or carbonate).Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation for another. Cationic exchange can be effected by direct contactof an aqueous solution of a salt of a compound of Formula I (e.g.,alkali or quaternary amine salt) with a solution containing the cationto be exchanged. This method is most effective when the desired saltcontaining the exchanged cation is insoluble in water and can beseparated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g., an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged for that of the original salt and the desiredproduct is eluted from the column. This method is particularly usefulwhen the desired salt is water-soluble, e.g., a potassium, sodium orcalcium salt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The synthesis of heterocyclic amines such as those represented byFormula III has been reviewed in "The Chemistry of HeterocyclicCompounds," a series published by Interscience Publ., New York andLondon. Aminopyrimidines are described by D. J. Brown in "ThePyrimidines," Vol. XVI of the series mentioned above which is hereinincorporated by reference. The 2-amino-1,3,5-triazines of Formula III,where A is A-1 and Z is N, can be prepared according to methodsdescribed by E. M. Smolin and L. Rapaport in "s-Triazines andDerivatives," Vol. XIII.

Pyrimidines of Formula III, where A is A-1 and Y is an acetal orthioacetal substituent, can be prepared by methods taught in EuropeanPatent Application No. 84,224 (published July 27, 1983).

Pyrimidines of Formula III, where A is A-1 and Y is cyclopropyl or OCF₂H can be synthesized according to the methods taught in U.S. Pat. No.4,515,626 and U.S. Pat. No. 4,540,782, respectively.

Compounds of Formula III, where A is A-2 or A-3, can be prepared byprocedures disclosed in U.S. Pat. No. 4,339,267.

Compounds of Formula III, where A is A-4, can be prepared by methodstaught in U.S. Pat. No. 4,487,626.

Additional references dealing with the synthesis of bicyclic pyrimidinesof Formula III, where A is A-2, A-3, or A-4 are Braker, Sheehan,Spitzmiller and Lott, J. Am. Chem. Soc., 69, 3072 (1947); Mitler andBhattachanya, Quart, J. Indian Chem. Soc., 4, 152 (1927); Shrage andHitchings, J. Org. Chem., 16, 1153 (1951); Caldwell, Kornfeld andDonnell, J. Am. Chem. Soc., 63, 2188 (1941); and Fissekis, Myles andBrown, J. Org. Chem., 29, 2670 (1964).

Compounds of Formula III, where A is A-5, can be prepared by methodstaught in U.S. Pat. No. 4,421,550.

Compounds of Formula III, where A is A-6, can be prepared by methodstaught in the U.S. Pat. No. 4,496,392.

The required sulfonamides of Formula IV, provided E is not oxygen, canbe conveniently prepared by amination of the corresponding sulfonylchlorides with ammonia or ammonium hydroxide by methods known to thoseskilled in the art. Alternatively deprotection of N-t-butylsulfonamideswith polyphosphoric acid (PPA) or trifluoroacetic acid (TFA) asdescribed by J. D. Lombardino, J. Org. Chem., 36, 1843 (1971) or J. D.Catt and W. L. Matier, J. Org. Chem., 39, 566 (1974), respectively,provides compounds of Formula IV.

In addition, deprotection of N-t-butyldimethylsilylsulfonamides withfluoride ion, provides sulfonamides of Formula IV, wherein E is notoxygen.

The intermediate sulfonyl chlorides of Formula X, as depicted inEquation 3, can be prepared from aromatic amines via a diazotizationprocess, as described in EPO Publication Nos. 83,975 and 85,476; or byoxidative chlorination of thiols or thioethers with chloride and wateras reviewed in Gilbert. "Sulfonation and Related Reactions," pp.202-214, Interscience Publishers, New York, 1965; when R₇ =H or benzyl,the oxidative chlorination may be effected by sodium hypochloritefollowing procedures described by L. H. McKendry and N. R. Pearson inSouth African Patent Application No. 84/8845 (November 13, 1984); or bymetal halogen exchange or directed lithiation of appropriatelysubstituted aryl or heterocyclic substrates followed by trapping withsulfuryl chloride. The lithiation can be performed according to theprocedure of S. H. Bhattacharya, et al., J. Chem. Soc. (C), 1265 (1968)or by procedures reviewed by H. Gschwend and H. Rodriquez in OrganicReactions, Vol. 26, Wiley, New York, 1979, and references cited within;or finally, when E is a CH₂ moiety, by a two step procedure involvingthe conversion of aromatic chloromethyl or bromomethyl compounds toisothiouronium salts, as described by Johnson and Spraque, J. Am. Chem.Soc., 58, 1348 (1936); 59, 1837 and 2439 (1937); 61, 176 (1939),followed by oxidative chlorination by the procedure of Johnson asdescribed in J. Am. Chem. Soc., 61, 2548 (1939) to provide the sulfonylchlorides X. ##STR18## wherein J is as previously defined provided E isnot oxygen,

G is H, NH₂, SR₇, Br, CH₂ Cl, CH₂ Br, and

R₇ is H, C₁ -C₃ alkyl, benzyl.

Amines of the Formula IX, wherein G is NH₂, can be prepared from thecorresponding nitro compounds by various reduction procedures asdescribed in U.S. Pat. Nos. 3,846,440 and 3,846,439 and in EP-A No.83,975 and references cited therein.

Phenols of Formula VII can be prepared from amines of Formula IX (G═NH₂)via a diazotization process, as described in A. I. Vogel, "PracticalOrganic Chemistry," P. 595 (1956), 3rd Ed; U.S. Pat. No. 3,270,029; J.H. Finley, et al., J. Het. Chem., 6, 841 (1969); and M. Ohta, et al., J.Pharm. Soc. Japan, 73, 701 (1953).

Compounds of the Formula XII, which serve as intermediates to compoundsof the Formula I as illustrated in Equations 1-3, can be prepared fromprecursors of the Formula XI by one or more of the procedures outlinedbelow. ##STR19## wherein Q and R₁ are as originally defined;

R₈ is H or CH₃, provided that when n is 2 or 3, R₈ is H;

m is 0 or 1, provided when m=1, n must be 0;

n is 0, 1, 2, or 3, provided that m and n cannot both be 0;

G is Cl, Br, CH₂ Cl, CH₂ Br, OH, NH₂, NO₂, SR₇, SO₂ NH₂, SO₂ NH-t-butylor SO₂ NHSi(CH₃)₂ -t-butyl;

M is Cl, Br, I, NH₂, NHOH, NHNH₂, COOCH₃, CONHNH₂, CN, COCl, CHO or Hsuitable leaving group, provided that when m=1, M is not Br or I;

R₇ is H, C₁ -C₃ alkyl or benzyl.

E₁ is O, S, SO, SO₂ or a single bond provided that when m=1, E₁ is asingle bond.

The ten procedures are based on established literature methodsprecedented by the references cited in Table 2. The references citedhave direct applicability to compounds of the Formula XII, wherein J isJ-1. However, the procedures and experimental methods described in thesereferences are equally applicable to the synthesis of compounds ofFormula XII, wherein J is J-2 through J-5, by analogous procedures orslight modifications thereof. The chemistry of the thiophene, pyridineand pyrazole ring systems has been revieved in "Chemistry ofHeterocyclic Compounds," Volumes 3, 14, and 5, respectively, Wiley, NewYork 1952 and later.

It should be noted that the chemical compatibility of the wide varietyof reactions and reaction conditions described throughout thisdisclosure with J, R₁, Q, and G must be taken into account and as suchrequires a judicious choice of the appropriate methods for preparingcompounds described within this disclosure. In addition, circumventionof instances of incompatibility may be achieved by the suitableselection of a protecting group, obvious to one skilled in the art. Fora compilation of references describing the wide variety of protectinggroups available, see T. W. Greene, "Protective Groups in OrganicSynthesis," John Wiley and Sons, Inc., New York, 1981.

The synthesis of the starting materials of Formula XI are known in thegeneral literature or can be prepared, by those skilled in the art, bysimple modifications of established routes.

Procedure 1: Direct N-alkylation of intact heterocyclic compounds,containing an N-H moiety, with compound substrates of the Formula XI,wherein m=0 and M is Cl, Bro or Iodine; or N-benzoylation ofheterocyclic, containing an N-H moiety, with benzoyl chlorides of theform XI, wherein m=1, M is Cl, and G is Cl, Br, CH₂ Cl, CH₂ Br, NO₂ orSR₇.

Procedure 2: C-alkylation of heterocyclic compounds containing an acidicC-H moiety, i.e., activated by a carbonyl or sulfonyl group, bysubstrates of the Formula XI wherein M is Cl, Br, or iodine; orC-benzoylation with benzoyl chlorides of the Formula XI, wherein m=1, Mis Cl, and G is Cl, Br, CH₂ Cl, CH₂ Br, NO₂ or SR₇.

Procedure 3: Reactions of derivatives of Formula XI, wherein M is NH₂,NHOH, or NHNH₂, as nucleophiles with bifunctional acyclic and cyclicreagents, which ultimately are converted to various Q values.

Procedure 4: Use of acid-derivatives of Formula XI, wherein M is COOCH₃,COHNNH₂, CN, or COCl; see Example 4.

Procedure 5: Synthesis from dianions derived from N-protected-(o-methylaromatic sulfonamides) of Formula XI, wherein M is H, n=1, R₈ =H, and Gis SO₂ NH-t-butyl or SO₂ NHSi(CH₃)₂ -t-butyl. These benzyl orbenzyl-like dianions can be prepared by reaction of the appropriatesulfonamide, as defined above, with two equivalents of n-butyllithium atlow temperatures in an inert solvent. In some instances, conversion ofthe lithium dianions of copper-lithium species is dictated by theliterature and can be accomplished by known procedures.

Procedure 6: Reactions of acyclic anions with aldehydes of the FormulaXI, wherein M is CHO (m=0). Further transformations, as described in thecited literature (Table 2) provide compounds of the Formula XII.

Procedure 7: Reactions of anions derived from aromatic heterocycles suchas thiophene, furan, pyrrole, and pyridine (or simple substitutedanalogues) which act as "masked" heterocycles of the form Q. Forexample, alkylation reactions of such anions with compounds of theFormula XI, wherein M is Cl, Br, or iodine, provide intermediates whichupon reduction (see for example conversions B and K in Table 1) yieldcompounds of the Formula XII.

Procedure 8: Synthesis of compounds of the Formula XII wherein M is avinyl group (m=0): see reference 37.

Procedure 9: This procedure involves the use of compounds which arerelated to XI, but are outside the defined limits of XI. These compoundsmay be prepared by literature procedures from compounds of the FormulaXI as defined. Additional functional group manipulation is thenrequired, the procedures of which are described in the references citedin Table 2, to convert these compounds to compounds of the Formula XII.

Procedure 10: This procedure is the conversion of the Q value, containedin the Formula XII to a different Q value. These conversion proceduresare summarized in Table 1. When applicable, the conversion procedures ofTable 1 are cited by their letter designations in Table 2.

                  TABLE 1                                                         ______________________________________                                        CONVERSION PROCEDURES                                                                Conversion                                                             Designation                                                                            From        To            References                                 ______________________________________                                        A        lactone     lactam        1-3                                        B        thiophene   tetrahydro    4-6                                                 furan       derivative                                                        pyrrole                                                              C        sulfide     sulfoxide or  7                                                               sulfone                                                  D        lactone, lactam,                                                                          α-unsaturated                                                                         8, 84                                               sulfone or  derivative                                                        sultam                                                               E        lactam      cyclic amine   9-11                                      F        cycloketone lactone       12-14                                      G        dihydro-γ-                                                                          tetrahydro-γ-                                                                         15-19                                               pyrone      pyrone                                                   H        dihydro-γ-                                                                          tetrahydro-γ-                                                                         20-22                                               pyridone    pyridone                                                 I        γ-pyrone                                                                            γ-pyridone                                                                            23-25                                      J        lactone     tetrahydrofuran                                                                             26                                                              or tetrahydropyran                                       K        pyridine    piperidine or 27-28                                               (including  N--substituted                                                    quaternary  piperidines                                                       salts)                                                               L        anhydride   succinimide                                              ______________________________________                                    

Table 2 summarizes selected synthetic procedures viable for thesynthesis of compounds of Formula XII. Table 2 is not meant to be allinclusive, but does provide synthetic routes, which are well establishedand precedented in the literature, through the known chemical procedures(1-10), conversions (A-L), and methods described in the references(1-84) or slight modifications thereof.

For example, the preparation of a compound of Formula XII, where Q is Q₁and X_(b) is NR₅ can be carried out according to the procedure outlinedin line number 2 of Table 2. Thus alkylation (procedure 2) ofbutyrolactone (QH=Q-1 where X_(b) =0) with an appropriately substitutedalkyl halide as described in references 29-31, followed by conversion inthe lactone moiety to a lactam (conversion procedure A) provides thedesired compound of Formula XII. Finally, compounds of Formula XII areconverted to the desired sulfonylureas of Formula I via one or more ofthe procedures outlined in Equation 1 through 3.

                                      TABLE 2                                     __________________________________________________________________________    Preparative Schemes for Compounds of the Formula XII                                                Conv..sup.3                                             No.                                                                              Q  X.sub.b                                                                          X.sub.c                                                                          Proc..sup.1                                                                       QH(X.sub.b(c)).sup.2                                                                Proc.                                                                             Ref.                                                                              Comments                                        __________________________________________________________________________    1  Q-1                                                                              O  -- 2   1(O)  --  29-31                                               2  Q-1                                                                              NR.sub.5                                                                         -- 2   1(O)  A   29-31                                               3  Q-1                                                                              NR.sub.5                                                                         -- 2   1(NR.sub.5)                                                                             32-35                                               4  Q-2                                                                              O  -- 5             36                                                  5  Q-2                                                                              NR.sub.5                                                                         -- 5         A   36                                                  6  Q-3                                                                              O     8             37                                                  7  Q-3                                                                              NR.sub.5                                                                            8         A   37                                                  8  Q-4                                                                              -- -- 1   4     --      See Example 1                                   9  Q-5                                                                              -- -- 2   5         38,39                                               10 Q-6      5   18        40-42                                                                             1,4-Addition                                    11 Q-7                                                                              -- -- 2             43-45                                               12 Q-8      9             38  Cyclize a halo-                                                               sulfonamide                                                                   with base                                       13 Q-9      9   --            Cyclize a halo-                                                               sulfonamide                                                                   with base                                       14 Q-10                                                                             -- -- 1   --        46  Analogous to                                                                  Example 1                                       15 Q-11  NR.sub.5                                                                         2             49                                                  16 Q-11  S  2             38,50                                               17 Q-11  SO 2         C   38,50                                               18 Q-11  SO.sub.2                                                                         2         C   38,50                                               19 Q-11                                                                             -- O  6             51,52                                               20 Q-12                                                                             -- NR.sub.5                                                                         2             49                                                  21 Q-12                                                                             -- S  9             53,54                                                                             See also ref 50                                 22 Q-12                                                                             -- SO 9         C   53,54                                                                             See also ref 50                                 23 Q-12                                                                             -- SO.sub.2                                                                         9         C   53,54                                                                             See also ref 50                                 24 Q-12                                                                             -- O  9             55                                                  25 Q-13  O  9             55                                                  26 Q-13  S  9             50,                                                                           52-54                                               27 Q-13  SO 9         C   50,                                                                           52-54                                               28 Q-13  SO.sub.2                                                                         9         C   50,                                                                           52-54                                               29 Q-13  NR.sub.5                                                                         5                 In addition to                                                                to appropriate                                                                pyrrolidinone                                                                 See also                                                                      ref. 56                                         30 Q-14                                                                             -- -- 1                 Protection of                                                                 co may be                                                                     necessary                                       31 Q-15                                                                             O  -- 5         D   36                                                  32 Q-15                                                                             NR.sub.5                                                                         -- 5         D,A 36  Conversion D                                                                  then A                                          33 G-16                                                                             O     8         D   37                                                  34 Q-16  NR.sub.5                                                                             8     D,A 37  Conversion D                                                                  then A                                          35 Q-17                                                                             -- -- 1   4     D       See example 1                                   36 Q-17                                                                             -- -- 1   17            See example 1                                   37 Q-18                                                                             -- -- 5   20    D   58-60                                                                             1,4 Addition to                                                               QH-18 followed                                                                by in situ                                                                    conversion D                                    38 Q-19                                                                             -- -- 1                 Use α, β                                                           unsaturated                                                                   propane                                                                       sultam                                          39 Q-20                                                                             O     2             29-31                                               40 Q-20                                                                             NR.sub.5                                                                            2             32-35                                                                             See ref 35, R = H                               41 Q-21                                                                             O     9             57  Ref 57                                                                        discusses                                                                     lactonization                                                                 of hydroxy-                                                                   acids                                           42 Q-21                                                                             NR.sub.5                                                                            9         D   57                                                  43 Q-22                                                                             O     9             57                                                  44 Q-22                                                                             NR.sub.5                                                                            9         A   57                                                  45 Q-23                                                                             O     2   5     F   38,39                                               46 Q-23                                                                             -- -- 2   5     F,A     Procedure E                                                                   then A                                          47 Q-24                                                                             -- -- 1   24            Modification                                                                  of example 1                                    48 Q-25                                                                             -- -- 2   25        37,39                                               49 Q-26     5             40-42                                                                             1,4 Addition                                    50 Q-26                                                                             -- '  9                 Cyclization of                                                                halo-                                                                         sulfonamides                                                                  with base                                       51 Q-27                                                                             -- -- 2   27        43-45                                               52 Q-28                                                                             -- -- 1                 Modification of                                                               Example 1                                       53 Q-29  NR.sub.5                                                                         2   29(NR.sub.5)                                                                            49                                                  54 Q-29  S  2,9           53,54,                                                                        58                                                  55 Q-29  SO 2,9       C   38,53,                                                                        54                                                  56 Q-29  SO.sub.2                                                                         2,9       C   38,53                                                                         54                                                  57 Q-29  O  2,9           38                                                  58 Q-30                                                                             -- O  5   41(O)     40-42                                                                             1,4 Addition                                    59 Q-30                                                                             -- NR.sub.5                                                                         5   41(NR.sub.5)                                                                            40-42                                                                             1,4 Addition                                    60 Q-30                                                                             -- S  5   41(S)     40-42                                                                             1,4 Addition                                    61 Q-30                                                                             -- SO 5   41(S) C   40-42                                                                             1,4 Addition                                    62 Q-30                                                                             -- SO.sub.2                                                                         5   41(S) C   40-42                                                                             1,4 Addition                                    63 Q-31                                                                             -- S  9   --        53-54                                               64 Q-31                                                                             -- SO 9   --    C   53-54                                               65 Q-31                                                                             -- SO.sub.2                                                                         9   --    C   53-54                                               66 Q-31                                                                             -- O  9   --    --  --                                                  67 Q-31                                                                             -- NR.sub.5                                                                         9   --    --  --                                                  68 Q-32                                                                             -- NR.sub.5                                                                         2   --    --  49                                                  69 Q-32                                                                             -- O  2             38  Modification                                                                  of ref. 49                                      70 Q-32                                                                             -- S  2             38  Modification                                                                  of ref. 49                                      71 Q-32                                                                             -- SO 2             38  Modification                                                                  of ref. 49                                      72 Q-32                                                                             -- SO.sub.2                                                                         2             38  Modification                                                                  of ref. 49                                      73 Q-33     1   33            C═O protection                                                            may be                                                                        necessary                                       74 Q-34  O  2   34(O)     38                                                  75 Q-34  S  2   34(S)     38                                                  76 Q-34  SO 2   34(S) C   38                                                  77 Q-34  SO.sub.2                                                                         2   34(S) C   38                                                  78 Q-34  NR.sub.5                                                                         2   34(NR.sub.5)                                                                            38                                                  79 Q-35  O  4         G   59                                                  80 Q-35  NR.sub.5                                                                         9         H   61                                                  81 Q-35  S  9             62                                                  82 Q-35  SO 9         C   62                                                  83 Q-35  SO.sub.2                                                                         9         C   62                                                  84 Q-36     1   36            C═O protection                                                            may be                                                                        necessary                                       85 Q-37                                                                             O     2   5     F,D 38,39                                               86 Q-37                                                                             NR.sub.5                                                                            2   5     F,D,A                                                                             38,39                                               87 Q-38                                                                             -- -- 2   38            Modification                                                                  of Example 1                                    88 Q-39                                                                             -- -- 2   25    D   38,39                                               89 Q-39                                                                             -- -- 2   39        38                                                  90 Q-40                                                                             -- -- 1                 Modification                                                                  of Example 1                                    91 Q-41  NR.sub.5                                                                         2   30(NR.sub.5)                                                                        D   49                                                  92 Q-41  O            D   38                                                  93 Q-41  S            D   38                                                  94 Q-41  SO           D,C 38                                                  95 Q-41  SO.sub.2     D,C 38                                                  96 Q-42  S  9         D   62                                                  97 Q-42  NR.sub.5                                                                         9             61                                                  98 Q-42  SO 9         D,C 62                                                  99 Q-42  SO.sub.2                                                                         9         D,C 6                                                   100                                                                              Q-42                                                                             -- O  2             38                                                  101                                                                              Q-43                                                                             -- -- 1   35    D                                                       102                                                                              Q-44                                                                             O  -- 9             63-65                                               103                                                                              Q-44                                                                             NR.sub.5                                                                         -- 9             63-65                                               104                                                                              Q-45     3                 Reaction of                                                                   amine with                                                                    γ-pyrone                                  105                                                                              Q-46     4             66                                                  106                                                                              Q-47     4             67-69                                                                             Ref 69 contains                                                               N--alkylation                                                                 procedures                                      107                                                                              Q-48     4             70                                                  108                                                                              Q-49     4             71                                                  109                                                                              Q-50     4             72-73                                               110                                                                              Q-51     4             74                                                  111                                                                              Q-52     4             75-77                                               112                                                                              Q-53     4             78                                                  113                                                                              Q-54     1   54        79,80                                               114                                                                              Q-55     1   55        81                                                  115                                                                              Q-56     1   56                                                            116                                                                              Q-57     9             82                                                  117                                                                              Q-58     8             83                                                  118                                                                              Q-59     1   59                                                            119                                                                              Q-60     1   60                                                            120                                                                              Q-61     9                                                                 121                                                                              Q-62     1   62                                                            122                                                                              Q-63     3                 M = NHOH                                        123                                                                              Q-64     2   64        38  R.sub.5 = 16                                    124                                                                              Q-65     1   65                                                            125                                                                              Q-66     2   66        38                                                  126                                                                              Q-67     1   67                                                            127                                                                              Q-68     2   68        38                                                  128                                                                              Q-69     1   69                                                            129                                                                              Q-69     3                 M = NHOH                                        130                                                                              Q-70     2   70        38                                                  131                                                                              Q-71     9                                                                 132                                                                              Q-72     1   72                                                            133                                                                              Q-73     1   73                                                            134                                                                              Q-74     1   74                                                            135                                                                              Q-75     6         L                                                       136                                                                              Q-76     1   76                                                            137                                                                              Q-77     6         L,D                                                     138                                                                              Q-78     6                 Anion from                                                                    CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.2 --                                        CO.sub.2 CH.sub.3 then                                                        ring close                                                                    with acid                                       139                                                                              Q-79     1   79                                                            140                                                                              Q-80     1   80                                                            141                                                                              Q-81     2   81        38                                                  142                                                                              Q-82     1   82                                                            143                                                                              Q-83     1   83                                                            144                                                                              Q-84     1   84                                                            145                                                                              Q-85     2   85        38                                                  146                                                                              Q-86     2   86        38                                                  147                                                                              Q-87     2   87        38                                                  __________________________________________________________________________     .sup.1 procedures of 1-10                                                     .sup.2 for example when QH(X.sub.b) = 1(O); QH is Q.sub.1, and X.sub.b is     oxygen which suggests butyrolactone would be a viable starting material       .sup.3 conversion procedures (A-L) are described in Table I.             

The preparation of the compounds of this invention is furtherillustrated by the following specific examples.

EXAMPLE 1 1-[(2-(Phenylmethylthio)phenylmethyl]-2-pyrrolidinone

To a solution of 1.35 g of potassium-tertbutoxide in 25 mL ofdimethylformamide, cooled to 0° C., was added 0.92 mL of2-pyrrolidinone. As a white precipitate formed, the mixture was stirredfor 10 minutes, and 3.0 g of 2-phenylmethylthio chloromethyl benzene wasadded in one portion. The resulting solution was allowed to warm to roomtemperature, stirred for 1 hour, poured into water, and extracted withmethylene chloride. The organic layer was washed well with water, driedover magnesium sulfate, filtered, and the filtrate evaporated to leave3.0 g of a yellow oil.

    ______________________________________                                        NMR (CDCl.sub.3) ppm:                                                                         7.3        (m, 9H, ArH)                                                       4.5        (s, 2H, CH.sub.2)                                                  4.0        (s, 2H CH.sub.2)                                                   3.05       (t, 2H, --CH.sub.2 --)                                             2.3        (t, 2H, --CH.sub.2 --)                                             1.7-2.05   (m, 2H, CH.sub.2)                                  ______________________________________                                    

EXAMPLE 2 2-(2-Oxo-1-pyrrolidinylmethyl)benzenesulfonamide

To a solution of 2.6 g of the compound of Example 1 dissolved in 100 mLof acetic acid, containing 0.5 mL of water, and cooled to 15° C., wasbubbled in chlorine gas for 15 minutes. A slight exotherm of 5° C. wasnoted. The reaction was stirred for an additional 5 minutes, poured intoice water, and extracted with methylene chloride. The organic layer waswashed with saturated sodium bicarbonate, dried over magnesium sulfate,filtered, and evaporated to an oil. The oil was immediately dissolved in100 mL of tetrahydrofuran and treated with 2 mL of concentrated ammoniumhydroxide and stirred for 1 hour. The tetrahydrofuran was removed on therotary-evaporator to give a semisolid. The residue was then trituratedwith water to form a sticky solid which was filtered off and trituratedwith ether to provide 1.1 g of an off-white solid; m.p. 149°-151° C. IR(Nujol) 1660(C=O) cm⁻¹

EXAMPLE 3N-[((4,6-dimethoxypyrimidin-2yl)aminocarbonyl)-2-(2-oxo-1-pyrrolidinylmethyl]-benzenesulfonamide

To a suspension of 254 mg of the product of Example 2 in 10 mL ofacetonitrile, containing 275 mg ofphenyl(4,6-dimethoxypyrimidin-2-yl)carbamate, was added 0.15 mL of1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resultant solution wasstirred for 2 hours, diluted with 20 mL of water and acidified with 5drops of concentrated hydrochloric acid. n-Butylchloride (10 mL) wasadded, stirred, and the white precipitate was filtered. The collectedwhite solid was washed with a little water, suction dried and finallydried in vacuo @ 70° C. overnight to afford 200 mg of a white solid,m.p. 185°-187° C.

IR (Nujol) 1730 (C=O); 1668 (C=O) cm⁻¹ ;

    ______________________________________                                        NMR (CDCl.sub.3) ppm                                                                           12.76      (bs, 1H, NH)                                                       8.21       (m, 1H, ArH)                                                       7.36-7.7   (m, 3H, ArH)                                                       7.22       (bs, 1H, NH)                                                       5.80       (s, 1H, PyH)                                                       5.01       (s, 2H, CH.sub.2)                                                  3.96       (s, 6H, OCH.sub.3)                                                 3.32       (t, 2H, CH.sub.2)                                                  2.46       (t, 2H, CH.sub.2)                                                  2.03       (m, 2H, CH.sub.2)                                 ______________________________________                                    

USE OF TABLES A, J, AND Q

For purposes of expediency and avoidance of voluminous pages of tableseach sulfonylurea is divided into three structural pieces as illustratedbelow. ##STR20##

Each structural piece A, J, and Q is fully defined separately in TablesA, J and Q respectively and requires the designation of a particularstructure from one of the structure(s) assigned to each of these tables.Thus to fully delineate a complete structure for a unique sulfonylureait requires the information from one entry in each of the tables A, J,and Q and a designation of one of these structures assigned to thattable. Note that only one structure, namely structure A, is assigned toTable A and need not be specifically designated.

The use of Tables A, J, and Q provides an alternative to listingindividual compounds line by line as is done in a conventional table. Itis the applicant's intent to specifically disclose each and everycompound that can be constructed from Tables A, J and Q using theprocedure described above and illustrated below.

The use of Tables A, J, and Q can be illustrated by the following. Forexample, specifically claimed is compound of Formula XIII and is##STR21## listed in Tables A, J, and Q as entry number 4 of Table A;entry number one of Table J--Structure B; and entry number seven ofTable Q--Structure J. As a shorthand notation, compound of Formula XIIIcan be listed in a matrix form as:

4; 1-B; 7-J

This provides a convenient method for listing the melting points ofcompounds as is done in the melting point table (AJQ) (see line numberone of Table AJQ). Each compound for which a melting point is availableis simply listed in the melting point table (AJQ) as the entry number ofTable A; entry number-structure for Table J; and entry number-structurefor Table Q in that order.

Also specifically claimed is compound of formula XIV shown below.##STR22##

Compound of Formula XIV is found in Tables A, J, and Q as entry numberfour of Table A; entry number one of Table J--Structure B; and entrynumber one of Table Q--Structure J or in the convenient matrix form as:

4; 1-B; 1-J

By analogy compounds of Formula XV and XVI having structures as shownbelow ##STR23## have matrix designations of 2; 1-B; 19-L and 4; 1-B;76-J respectively.

The structures assigned to Tables A, J, and Q are shown below followedby Tables A, J, and Q and finally in the melting point Table AJQ.

    ______________________________________                                        STRUCTURE FOR TABLE A                                                         ______________________________________                                                 ##STR24##                                                            ______________________________________                                        STRUCTURES FOR TABLE J                                                        ______________________________________                                                 ##STR25##                                                            C                                                                                      ##STR26##                                                            D                                                                                      ##STR27##                                                            E                                                                                      ##STR28##                                                            F                                                                                      ##STR29##                                                            G                                                                                      ##STR30##                                                            H                                                                                      ##STR31##                                                            I                                                                                      ##STR32##                                                            ______________________________________                                        STRUCTURES FOR TABLE Q                                                        ______________________________________                                        J       CH.sub.2 Q                                                                     ##STR33##                                                            L       CH.sub.2 CH.sub.2Q                                                    M                                                                                      ##STR34##                                                            N       SCH.sub.2 Q                                                           O                                                                                      ##STR35##                                                            P       SO.sub.2 CH.sub.2 Q                                                   Q       OCH.sub.2 Q                                                           ______________________________________                                    

    ______________________________________                                        TABLE A FOR STRUCTURE A                                                       Entry      X           Y            Z                                         ______________________________________                                        1          CH.sub.3    CH.sub.3     CH                                        2          CH.sub.3    OCH.sub.3    CH                                        3          CH.sub.3    OCH.sub.3    N                                         4          OCH.sub.3   OCH.sub.3    CH                                        5          OCH.sub.3   OCH.sub.3    N                                         6          Cl          OCH.sub.3    CH                                        7          CH.sub.3    C.sub.2 H.sub.5                                                                            CH                                        8          CH.sub.3    CH.sub.2 OCH.sub.3                                                                         CH                                        9          CH.sub.3    CH.sub.2 OCH.sub.3                                                                         N                                         10         CH.sub.3    NHCH.sub.3   CH                                        11         CH.sub.3    NHCH.sub.3   N                                         12         CH.sub.3    CH(OCH.sub.3).sub.2                                                                        CH                                        13         CH.sub.3    CH(OCH.sub.3).sub.2                                                                        N                                         14         CH.sub.3    Cyclopropyl  CH                                        15         CH.sub.3    Cyclopropyl  N                                         16         OCH.sub.3   C.sub.2 H.sub.5                                                                            CH                                        17         OCH.sub.3   C.sub.2 H.sub.5                                                                            N                                         18         OCH.sub.3   CH.sub.2 OCH.sub.3                                                                         CH                                        19         OCH.sub.3   CH.sub.2 OCH.sub.3                                                                         N                                         20         OCH.sub.3   NHCH.sub.3   CH                                        21         OCH.sub.3   NHCH.sub.3   N                                         22         OCH.sub.3   CH(OCH.sub.3).sub.2                                                                        CH                                        23         OCH.sub.3   CH(OCH.sub.3).sub.2                                                                        N                                         24         OCH.sub.3   Cyclopropyl  CH                                        25         OCH.sub.3   Cyclopropyl  N                                         26         OCH.sub.2 CH.sub.3                                                                        CH.sub.3     CH                                        27         OCH.sub.2 CH.sub.3                                                                        CH.sub.3     N                                         28         OCH.sub.2 CH.sub.3                                                                        OCH.sub.3    CH                                        29         OCH.sub.2 CH.sub.3                                                                        OCH.sub.3    N                                         30         OCH.sub.2 CH.sub.3                                                                        CH.sub.2 OCH.sub.3                                                                         CH                                        31         OCH.sub.2 CH.sub.3                                                                        CH.sub.2 OCH.sub.3                                                                         N                                         32         OCH.sub.2 CH.sub.3                                                                        NHCH.sub.3   CH                                        33         OCH.sub.2 CH.sub.3                                                                        NHCH.sub.3   N                                         34         OCH.sub.2 CH.sub.3                                                                        CH(OCH.sub.3).sub.2                                                                        CH                                        35         OCH.sub.2 CH.sub.3                                                                        CH(OCH.sub.3).sub.2                                                                        N                                         36         Cl          OCF.sub.2 H  CH                                        37         OCF.sub.2 H CH.sub.3     CH                                        38         OCF.sub.2 H OCH.sub.3    CH                                        39         OCF.sub.2 H C.sub.2 H.sub.5                                                                            CH                                        40         OCF.sub.2 H CH.sub.2 OCH.sub.3                                                                         CH                                        41         OCF.sub.2 H NHCH.sub.3   CH                                        42         OCF.sub.2 H CH(OCH.sub.3).sub.2                                                                        CH                                        43         OCF.sub.2 H Cyclopropyl  CH                                        ______________________________________                                    

    ______________________________________                                        TABLE J FOR STRUCTURES B-I.sup.a                                                                      R.sub.1                                                                       No. refers to position                                Entry      E            in Structure B only                                   ______________________________________                                        1          --           H                                                                (Single bond)                                                      2          --           5-CH.sub.3                                            3          --           5-CH.sub.2 Cl                                         4          --           5-OCH.sub.3                                           5          --           5-SCH.sub.3                                           6          --           5-SCH.sub.2 CH.sub.3                                  7          --           5-Cl                                                  8          --           6-F                                                   9          --           5-NO.sub.2                                            10         --           6-SO.sub.2 N(CH.sub.3).sub.2                          11         --           5-SOCH.sub.3                                          12         --           3-Cl                                                  13         --           6-SO.sub.2 CH.sub.3                                   14         --           5-CH.sub.2 CN                                         15         --           5-CN                                                  16         --           6-CN                                                  17         --           5-CO.sub.2 CH.sub.3                                   18         --           5-CF.sub.3                                            19         CH.sub.2     H                                                     20         CH.sub.2     5-CN                                                  21         CH.sub.2     5-SCH.sub.3                                           22         CH.sub.2     5-OCH.sub.3                                           23         CH.sub.2     5-Cl                                                  24         O            H                                                     25         O            5-SCH.sub.3                                           ______________________________________                                         .sup.a W = O, R = H                                                      

    ______________________________________                                        TABLE Q FOR STRUCTURES J-Q                                                                                             Proviso                                                                       (See end of                          Entry  Q       X.sub.b X.sub.c                                                                             R.sub.5                                                                              R.sub.6                                                                            Table)                               ______________________________________                                        1      Q-1     O       --    --     --   a                                    2      Q-1     NR.sub.5                                                                              --    CH.sub.3                                                                             --   --                                   3      Q-2     O       --    --     --   --                                   4      Q-2     NR.sub.5                                                                              --    CH.sub.3                                                                             --   --                                   5      O-3     O       --    --     --   --                                   6      Q-3     NR.sub.5                                                                              --    CH.sub.3                                                                             --   --                                   7      Q-4     --      --    --     --   --                                   8      Q-5     --      --    --     --   --                                   9      Q-6     --      --    --     --   --                                   10     Q-7     --      --    CH.sub.3                                                                             --   --                                   11     Q-8     --      --    CH.sub.3                                                                             --   --                                   12     Q-9     --      --    CH.sub.3                                                                             --   --                                   13     Q-10    --      --    --     --   --                                   14     Q-11    --      O     --     --   --                                   15     Q-11    --      NR.sub.5                                                                            CH.sub.2 CH.sub.3                                                                    --   --                                   16     Q-12    --      NR.sub.5                                                                            CH.sub.2 CH.sub.3                                                                    --   --                                   17     Q-12    --      O     --     --   --                                   18     Q-13    --      O     --     --   --                                   19     Q-14    --      --    --     --   --                                   20     Q-15    O       --    --     --   --                                   21     Q-15    NR.sub.5                                                                              --    CH.sub.3                                                                             --   --                                   22     Q-16    O       --    --     --   b                                    23     Q-16    NR.sub.5                                                                              --    CH.sub.3                                                                             --   b                                    24     Q-17    --      --    --     --   --                                   25     Q-18    --      --    --     --   --                                   26     Q-19    --      --    --     --   --                                   27     Q-20    O       --    --     --   --                                   28     Q-20    NR.sub.5                                                                              --    CH.sub.3                                                                             --   --                                   29     Q-21    O       --    --     --   --                                   30     Q-22    O       --    --     --   --                                   31     Q-23    O       --    --     --   --                                   32     Q-23    NR.sub.5                                                                              --    CH.sub.3                                                                             --   --                                   33     Q-24    --      --    --     --   --                                   34     Q-25    --      --    --     --   --                                   35     Q-26    --      --    CH.sub.3                                                                             --   --                                   36     Q-27    --      --    CH.sub.3                                                                             --   --                                   37     Q-28    --      --    --     --   --                                   38     Q-29    --      NR.sub.5                                                                            CH.sub.3                                                                             --   --                                   39     Q-30    --      O     --     --   --                                   40     Q-31    --      O     --     --   --                                   41     Q-32    --      NR.sub.5                                                                            CH.sub.3                                                                             --   --                                   42     Q-33    --      --    --     --   --                                   43     Q-33    --      O     --     --   --                                   44     Q-34    --      NR.sub.5                                                                            CH.sub.3                                                                             --   --                                   45     Q-35    --      O     --     --   --                                   46     Q-36    --      --    --     --   --                                   47     Q-37    O       --    --     --   b                                    48     Q-38    NR.sub.5                                                                              --    CH.sub.3                                                                             --   --                                   49     Q-38    --      --    --     --   --                                   50     Q-39    --      --    --     --   --                                   51     Q-40    --      --    --     --   --                                   52     Q-41    --      NR.sub.5                                                                            CH.sub.3                                                                             --   b                                    53     Q-41    --      O     --     --   b                                    54     Q-42    --      O     --     --   b                                    55     Q-42    --      NR.sub.5                                                                            --     --   b                                    56     Q-43    --      --    --     --   --                                   57     Q-44    --      O     --     --   b                                    58     Q-44    --      NR.sub.5                                                                            CH.sub.3                                                                             --   b                                    59     Q-45    --      --    --     --   b                                    60     Q-46    --      --    CH.sub.3                                                                             --   b                                    61     Q-46    --      --    H      --   b                                    62     Q-47    --      --    CH.sub.3                                                                             --   b                                    63     Q-48    --      --    CH.sub.3                                                                             --   b                                    64     Q-49    --      --    CH.sub.3                                                                             --   b                                    65     Q-50    --      --    CH.sub.3                                                                             CH.sub.3                                                                           b                                    66     Q-51    --      --    --     --   b                                    67     Q-52    --      --    --     --   b                                    68     Q-53    --      --    --     CH.sub.3                                                                           b                                    69     Q-54    --      --    --     --   --                                   70     Q-54    --      --    --     --   a                                    71     Q-55    --      --    --     --   a                                    72     Q-56    --      --    --     --   --                                   73     Q-57    --      --    CH.sub.3                                                                             --   --                                   74     Q-58    --      --    H      --   --                                   75     Q-58    --      --    CH.sub.3                                                                             --   --                                   76     Q-59    --      --    --     --   --                                   77     Q-60    --      --    CH.sub.3                                                                             --   --                                   78     Q-61    --      --    CH.sub.3                                                                             CH.sub.3                                                                           --                                   79     Q-62    --      --    CH.sub.3                                                                             --   --                                   80     Q-63    --      --    --     --   --                                   81     Q-63    --      --    --     --   c                                    82     Q-64    --      --    CH.sub.3                                                                             --   --                                   83     Q-65    --      --    --     --   --                                   84     Q-66    --      --    CH.sub.3                                                                             --   --                                   85     Q-67    --      --    --     --   --                                   86     Q-68    --      --    CH.sub.3                                                                             --   --                                   87     Q-69    --      --    --     --   --                                   88     Q-70    --      --    CH.sub.3                                                                             --   --                                   89     Q-71    --      --    --     --   --                                   90     Q-72    --      --    CH.sub.3                                                                             --   --                                   91     Q-73    --      --    CH.sub.3                                                                             --   --                                   92     Q-74    --      --    --     --   --                                   93     Q-75    --      --    CH.sub.3                                                                             --   --                                   94     Q-76    --      --    --     --   --                                   95     Q-77    --      --    CH.sub.3                                                                             --   b                                    96     Q-78    --      --    --     --   --                                   97     Q-79    --      --    --     --   --                                   98     Q-80    --      --    --     --   --                                   99     Q-81    --      --    CH.sub.3                                                                             --   --                                   100    Q-82    --      --    --     --   --                                   101    Q-83    --      --    --     --   --                                   102    Q-84    --      --    CH.sub.3                                                                             --   --                                   103    Q-85    --      --    --     --   --                                   104    Q-86    --      --    --     --   --                                   105    Q-87    --      --    --     --   --                                   ______________________________________                                         a Q.sub.1 is substituted by a 4methyl group                                   b Structure B of Table J is excluded with the use of the Q value              designated in this entry                                                      c Substituted by α,α-dimethyl                                

    ______________________________________                                        MELTING POINT TABLE (AJQ)                                                     DE-        TABLE A:  TABLE J:    TABLE Q                                      SIGNATIONS:                                                                              ENTRY #:  ENTRY #-    ENTRY #-                                                          STRUCTURE   STRUCTURE                                    No.        Matrix Designation                                                                          MP °C.                                        ______________________________________                                         1         4; 1-B; 7-J   185-87                                                2         5; 1-B; 7-J   194-95                                                3         1; 1-B; 72-J  184-85                                                4         4; 1-B; 72-J  139-42                                                5         5; 1-B; 72-J  184-85                                                6         1; 1-B; 70-J  192-94                                                7         2; 1-B; 70-J  177-78                                                8         4; 1-B; 70-J  183-85                                                9         6; 1-B; 70-J  202-04                                               10         3; 1-B; 70-J  185-86                                               11         5; 1-B; 70-J  195-96                                               12         2; 1-B; 1-J     202-04.5                                           13         6; 1-B; 1-J     178-82.5                                           14         1; 1-B; 1-J   193-96                                               15         5; 1-B; 1-J   182-85                                               16         3; 1-B; 1-J   188-94                                               17         4; 1-B; 1-J   178-82                                               18         1; 1-E; 7-J   174-76                                               19         2; 1-E; 7-J   163-65                                               20         4; 1-E; 7-J   137-39                                               21         6; 1-E; 7-J   182-83                                               22         3; 1-E; 7-J   171-72                                               23         5; 1-E; 7-J   169-71                                               24         1; 1-E; 72-J  159-61                                               25         2; 1-E: 72-J  146-55                                               26         4; 1-E; 72-J  157-60                                               27         6; 1-E; 72-J  146-50                                               28         3; 1-E; 72-J  155-61                                               29         1; 1-E; 70-J  190-91                                               30         2; 1-E; 70-J  169-72                                               31         4; 1-E; 70-J  129-31                                               32         6; 1-E; 70-J  168-75                                               33         3; 1-E; 70-J  154-59                                               34         5; 1-E; 70-J  170-73                                               35         4; 1-E; 33-J  150-60                                               36         5; 1-E; 33-J  170-72                                               ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

    ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts         1-25      70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, New Jersey, but other solids, either mined or manufactured,may be used. The more absorptive diluents are preferred for wettablepowders and the denser ones for dusts. Typical liquid diluents andsolvents are described in Marsden, "Solvents Guide," 2nd Ed.,Interscience, New York, 1950. Solubility under 0.1% is preferred forsuspension concentrates; solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well asSisely and Wood, "Encyclopedia of Surface Active Agents", ChemicalPublishing Co., Inc., New York, 1964, list surfactants and recommendeduses. All formulations can contain minor amounts of additives to reducefoaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8--57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167, and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 4

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-                                                    80%                                               oxo-1-pyrrolidinylmethyl)benzenesulfonamide                                   sodium alkylnaphthalenesulfonate                                                                          2%                                                sodium ligninsulfonate      2%                                                synthetic amorphous silica  3%                                                kaolinite                   13%                                               ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 5

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[[4-methoxy-6-methyl-1,3,5-triazin-2-yl)-                                                             50%                                                aminocarbonyl]-2-(2-oxo-1-pyrrolidinylmethyl)-                                benzenesulfonamide                                                            sodium alkylnaphthalenesulfonate                                                                          2%                                                low viscosity methyl cellulose                                                                            2%                                                diatomaceous earth         46%                                                ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 6

    ______________________________________                                        Granule                                                                       ______________________________________                                        Wettable Powder of Example 5                                                                          5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules while tumbling in a double-cone blender.The granules are dried and packaged.

EXAMPLE 7

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        N--[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-                                                     25%                                              oxo-1-pyrrolidinylmethyl)benzenesulfonamide                                   anhydrous sodium sulfate     10%                                              crude calcium ligninsulfonate                                                                               5%                                              sodium alkylnaphthalenesulfonate                                                                            1%                                              calcium/magnesium bentonite  59%                                              ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 8

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        N--[[1-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar-                                                     25%                                                bonyl]-2-(2-oxo-1-pyrrolidinylmethyl)benzene-                                 sulfonamide                                                                   polyoxyethylene sorbitol hexaoleate                                                                       5%                                                highly aliphatic hydrocarbon oil                                                                         70%                                                ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 9

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-                                                      20%                                                 carbonyl]-2- 2-oxo-1-pyrrolidinylmethyl)-                                     benzenesulfonamide                                                            sodium alkylnaphthalenesulfonate                                                                        4%                                                  sodium ligninsulfonate    4%                                                  low viscosity methyl cellulose                                                                          3%                                                  attapulgite               69%                                                 ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 10

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        N--[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-                                                    1%                                                oxo-1-pyrrolidinylmethyl)benzenesulfonamide                                   N,N--dimethylformamide      9%                                                attapulgite granules        90%                                               (U.S.S. 20-40 sieve)                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 11

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        N--[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-                                                       40%                                                carbonyl]-2-(2-oxo-1-pyrrolidinylmethyl)benzene-                              sulfonamide                                                                   polyacrylic acid thickener                                                                              0.3%                                                dodecylphenol polyethylene glycol ether                                                                 0.5%                                                disodium phosphate          1%                                                monosodium phosphate      0.5%                                                polyvinyl alcohol           1%                                                water                     56.7%                                               ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 12

    ______________________________________                                        Solution                                                                      ______________________________________                                        N--[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-                                                      5%                                              oxo-1-pyrrolidinylmethyl)benzenesulfonamide,                                  sodium salt                                                                   water                        95%                                              ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 13

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        N--[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar-                                                      0.1%                                             bonyl]-2-(2-oxo-1-pyrrolidinylmethyl)benzene-                                 sulfonamide                                                                   attapulgite granules        99.9%                                             (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 14

    ______________________________________                                        Granule                                                                       ______________________________________                                        N--[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-                                                     80%                                              oxo-1-pyrrolidinylmethyl)benezenesulfonamide                                  wetting agent                 1%                                              crude ligninsulfonate salt (containing                                                                     10%                                              5-20% of the natural sugars)                                                  attapulgite clay              9%                                              ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 15

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        N--[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-                                                     99%                                              oxo-1-pyrrolidinylmethyl)benzenesulfonamide                                   silica aerogel               0.5%                                             synthetic amorphous silica   0.5%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 16

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-                                                     90%                                              oxo-1-pyrrolidinylmethyl)benzenesulfonamide                                   dioctyl sodium sulfosuccinate                                                                              0.1%                                             synthetic fine silica        9.9%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 17

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-                                                       40%                                                carbonyl]-2-(2-oxo-1-pyrrolidinylmethyl)-                                     benzenesulfonamide                                                            sodium ligninsulfonate     20%                                                montmorillonite clay       40%                                                ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 18

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        N--[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-                                                     35%                                              oxo-1-pyrrolidinylmethyl)benzenesulfonamide                                   blend of polyalcohol carboxylic                                                                             6%                                              esters and oil soluble petroleum                                              sulfonates                                                                    xylene                       59%                                              ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 19

    ______________________________________                                        Dust                                                                          ______________________________________                                        N--[[(4-methoxy-6-methyl-1,3,4-triazin-2-yl)amino-                                                       10%                                                carbonyl]-2-(2-oxo-1-pyrrolidinylmethyl)-                                     benzenesulfonamide                                                            attapulgite                10%                                                Pyrophyllite               80%                                                ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

Utility

Test results indicate that the compounds of the present invention arehighly active preemergent or postemergent herbicides or plant growthregulants. Many of them have utility for broad-spectrum pre- and/orpost-emergence weed control in areas where complete control of allvegetation is desired, such as around fuel storage tanks, ammunitiondepots, industrial storage areas, parking lots, drive-in theaters,around billboards, highway and railroad structures. Some of thecompounds have utility for selective weed control in crops such aswheat, second barley. Alternatively, the subject compounds are useful tomodify plant growth.

The rates of application for the compounds of the invention aredetermined by number of factors, including their use as plant growthmodifiers or as herbicides, the crop species involved, the types ofweeds to be controlled, weather and climate, formulations selected, modeof application, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.005 to 10kg/ha, the lower raters being suggested for use on lighter soils and/orthose having a low organic matter content, for plant growth modificationor for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide, examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

    ______________________________________                                        COMPOUNDS                                                                     COMPOUND  Q              X       Y     Z                                      ______________________________________                                         ##STR36##                                                                               ##STR37##     OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     2                                                                                        ##STR38##     OCH.sub.3                                                                             OCH.sub.3                                                                           N                                      3                                                                                        ##STR39##     CH.sub.3                                                                              CH.sub.3                                                                            CH                                     4                                                                                        ##STR40##     OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     5                                                                                        ##STR41##     OCH.sub.3                                                                             OCH.sub.3                                                                           N                                      6                                                                                        ##STR42##     CH.sub.3                                                                              CH.sub.3                                                                            CH                                     7                                                                                        ##STR43##     CH.sub.3                                                                              OCH.sub.3                                                                           CH                                     8                                                                                        ##STR44##     Cl      OCH.sub.3                                                                           CH                                     9                                                                                        ##STR45##     CH.sub.3                                                                              OCH.sub.3                                                                           CH                                     10                                                                                       ##STR46##     OCH.sub.3                                                                             OCH.sub.3                                                                           N                                      11                                                                                       ##STR47##     CH.sub.3                                                                              OCH.sub.3                                                                           N                                      12                                                                                       ##STR48##     OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     ______________________________________                                         ##STR49##                                                                    13                                                                                       ##STR50##     CH.sub.3                                                                              OCH.sub.3                                                                           CH                                     14                                                                                       ##STR51##     OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     15                                                                                       ##STR52##     Cl      OCH.sub.3                                                                           CH                                     16                                                                                       ##STR53##     CH.sub.3                                                                              CH.sub.3                                                                            CH                                     17                                                                                       ##STR54##     CH.sub.3                                                                              OCH.sub.3                                                                           CH                                     18                                                                                       ##STR55##     OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     19                                                                                       ##STR56##     Cl      OCH.sub.3                                                                           CH                                     20                                                                                       ##STR57##     CH.sub.3                                                                              OCH.sub.3                                                                           N                                      21                                                                                       ##STR58##     CH.sub.3                                                                              OCH.sub.3                                                                           CH                                     22                                                                                       ##STR59##     OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     ______________________________________                                    

Test A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), cheatgrass (Bromus secalinus),velvetleaf (Abutilon theophrasti), morningglory (Ipomea spp.), cocklebur(Xanthium pensylvanicum), sorghum, corn, soybean, sugarbeet, cotton,rice, wheat, and purple nutsedge (Cyperus rotundus) tubers were plantedand treated preemergence with the test chemicals dissolved in anon-phytotoxic solvent. At the same time, these crop and weed specieswere treated with a soil/foliage application. At the time of treatment,the plants ranged in height from 2 to 18 cm. Treated plants and controlswere maintained in a greenhouse for sixteen days, after which allspecies were compared to controls and visually rated for response totreatment. The ratings, summarized in Table A, are based on a numericalscale extending from 0=no injury, to 10=complete kill. The accompanyingdescriptive symbols have the following meanings:

C=chlorosis/necrosis;

B=burn;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effect;

U=unusual pigmentation;

X=axillary stimulation;

S=albinism; and

6Y=abscised buds or flowers.

    TABLE A      Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. 8 Cmpd. 9 C     mpd. 10 Cmpd. 11 Compound 12 Cmpd. 13 Cmpd. 14 Cmpd. 15 Rate (kg/ha)     0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.01 0.05     0.05 0.05       POSTEMERGENCE Morningglory 10C 1C,1H 9C 10C 2C,6G 2C,5G 5C,9G 4C,9G     10C 4C,8G 6C,9G 9C 2G 10C 10C 5C,9G Cocklebur 10C 1C 5C,9G 9C 2C,3H     3C,9H 6C,9G 5C,9G 10C 4C,9G 4C,9G 10C 2C,9H 9C 9C 5C,9H Velvetleaf 9C 0     2C,6G 10C 0 3G 3C,8H 5G 4C,9G 4C,8H 4C,9G 10C 5C,9G 4C,8G 9C 2G Nutsedge     3C,8G,9X 0 5G 3C,9G 0 2C,4G 5G 2G 0 0 0 6G 2G 4G 4C,8G 0 Crabgrass 4C,9G     0 5C,9G 3C,9H 0 0 3G 0 3G 0 0 0 0 0 0 0 Giant Foxtail         4G 0 0 2G     0 4G 4C,9G 0 Barnyardgrass 9C 0 9C 9C 3C,8H 3C,5H 3C,8H 0 2C,8G 1C 0 7H     3H 8H 10C 5H Cheatgrass 9C 0 8G 7G 0 6G 2C,8G 0 2C,8G 0 0 7G 6G 0 7G 0     Wild Oats 4C,8G 2C,2H 9C 4C,8G 4C,8G 6G 2C,5G 0 5G 0 0 0 0 3C,6G 0 0     Wheat 3G 0 9C 0 0 4G 2C,5G 0 4G 0 0 5G 0 4G 0 0 Corn 5U,9G 8G 10C 6C,9G     5C,9G 3C,7H 3C,9G 0 3C,7G 1H 0 1H 0 3C,8H 9G 4G Barley         2C,7G 0 0     7G 3G 0 2C 0 Soybean 9C 3C 9C 6C,9G 4C,8G 5C,9G 9C 3C,8G 5H 0 0 2C,8G 5H     5C,9G 9C 3C,8G Rice 9C 5G 6C,9G 9C 4C,8G 5G 3C,8G 5G 7G 0 2G 8G 3G 2C,6G     2C,9G 6G Sorghum 9C 4G 9C 5C,9G 3C,6H 4C,8H 2C,9G 3C,7G 2C,9G 2C,5G 4G     2C,8H 7G 3C,8H 4C,9G 4C,9H Sugar beet 9C 3C,3H 9C 9C 4C,7G 2H 3C,5G 2H     3C,7G 9C 9C 9C 5C,9G 10C 10C 4C,8G Cotton 9C 2C,2H 5C,9G 9C 4C,6G 4C,8H     3C,6G 5G 9C 8G 2C,9G 3C,9G 4C,8G 5C,9G 9C 3C,7G  PREEMERGENCE Morningglor     y 9G 2H 8H 9G 3G 7H 9G 3G 9G 5G 9C 5G 5G 8G 9G 8G Cocklebur 9H 2H 9H 9H     3G 2H 9H 9G -- 9H -- -- 7G 9H 9H -- Velvetleaf 9C 7G 7G 8G 0 3G 9C 0 10C     9C 2G 7G 6G 9G 9G 7G Nutsedge 8G 0 4G 9G 8G 0 3G 0 0 0 0 4G 0 0 5G 0     Crabgrass 2C,6G 2G 2G 9G 0 4G 2G 0 7G 0 0 0 0 4G -- -- Giant Foxtail         5G 0 0 4G 2C 2G 6G 3G Barnyardgrass 4C,9H 2G 2C,9H 5C,9H 2C 0 2C,5G     0 2C,8G 2C 0 2C,7G 2C 2G 8G 2G Cheatgrass 5C,9H 0 7H 2C,7G 0 7G 8G 0 7G     0 0 9H 7G 0 7G 0 Wild Oats 4C,9G 0 9C 3C,8G 0 0 2C,6G 0 5G 0 0 0 0 0 0 0     Wheat 4C,8G 0 9H 7G 0 0 7G 2G 5G 0 0 0 0 0 0 0 Corn 4C,9H 2G 4C,9H 3U,9H     2C,5G 0 2C,8H 2G 2C,7G 0 0 6G 5G 3C,7H 3C,8G 3G Barley         8G 0 0 7G     0 0 5G 0 Soybean 3C,7G 0 5G 4C,8H 2G 10E 3C,6H 2H 2G 2G 2C,5G 0 0 3C,7H     9H 0 Rice 10E 0 10E 10E 7G 0 3C,7H 0 7G 2G 0 6G 0 3G 6G 3G Sorghum 10E 0     10E 4C,9H 2C,6G 3G 3C,9H 2C 2C,8G 3G 4G 2C,8H 3G 4G 4C,9H 0 Sugar beet     5C,9G  10E 10C 10C 8G 4C,9G 6G 8G 7G 4C,8G 8G 5G 10C 10C 8G Cotton 4C,9G     0 8G 5C,9G 0 0 5G 0 7G 4G 5G 5G -- 3C,7G 9G 8G        Cmpd. 16 Cmpd. 17 Cmpd. 18 Cmpd. 19 Cmpd. 20 Cmpd. 21 Cmpd. 22 Rate     kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05       POSTEMERGENCE Morningglory 10C 10C 10C 10C 4C,8H 10C 4C,9G Cocklebur     10C 10C 10C 10C 4C,9G 9C 4C,9H Velvetleaf 5G 4C,9G 9C 3C,7G 3C,7H 4C,8G     4C,8G Nutsedge 2C,9G 3C,7G 5C,9G 4G 0 2C 2G Crabgrass 6G 2G 3G 3G 0 3G     2G Giant Foxtail 5C,9G 4C,8G 3C,8G 3C,5G 2C,8G 2G 0 Barnyardgrass 10C     4C,9H 4C,9H 3C,8H 5C,9H 2C,5H 0 Cheatgrass 9G 7G 4C,9G 3C,6G 0 0 0 Wild     Oats 3G 0 0 0 0 0 0 Wheat 3G 3G 0 2G 0 0 0 Corn 9C 9C 10C 9H 10C 8H 3H     Barley 2C,5G 0 0 0 0 0 0 Soybean 4C,9G 4C,9G 9C 4C,9G 2C,7G 4C,9G 4C,9G     Rice 9C 5C,9G 8G 8G 7G 5G 4G Sorghum 4C,9G 4C,9H 9H 4C,9H 4C,9H 3C,8G 2G     Sugar beet 10C 10C 10C 9C 4C,8H 3C,7G 2C,6G Cotton 4C,9G 10C 10C 10C     3C,7G 4C,8H 3C,6G PREEMERGENCE Morningglory 9G 9G 9G 8G 7H 9G 7H     Cocklebur 9H 9H 9H 8H 7G 9H 7H Velvetleaf 9G 9G 9G 9G 0 8G 7G Nutsedge     9G 8G 10E 9G 0 0 0 Crabgrass 6G 5G 5G 2G 0 3G -- Giant Foxtail 3C,7G     3C,7G 3C,7G 2C,4G 0 3G 0 Barnyardgrass 3C,9H 4C,9H 9H 3C,7G 0 0 0     Cheatgrass 8G 8G 9H 5G 0 0 0 Wild Oats 5G 5G 4G 0 0 0 0 Wheat 4G 2G 0 0     0 0 0 Corn 9H 3C,9H 3C,9H 7G 7G 5G 0 Barley 2C,8G 5G 6G 0 0 0 0 Soybean     7H 9H 9H 0 0 3C,6H 2C,4H Rice 4C,8H 8G 8G 5G 5G 2C,5G 0 Sorghum 8G 3C,8G     7G 6G 0 2C,4G 2C Sugar beet 10E 10E 10E 4C,9G 9C 8G 8G Cotton 9G 9G 9G     2C,8G 4G 2C,6G 7G

REFERENCES

1. Scott and Kearse, J. Org. Chem., 5, 598 (1940).

2. Jones et. al., J. Am. Chem. Soc., 48, 181 (1926).

3. Jones et. al., IBID., 49, 2528 (1927).

4. Z. N. Parnes et al., Izv. Akad. Nauk SSSR, Ser. Khim., (11) 2526(1977); CA., 88 62239k.

5. E. Spath and F. Kuffner., Ber., 68, 2238 (1936).

6. D. S. Tarbell and C. Weaver, J. Am. Chem. Soc., 63, 2939 (1941).

7. H. O. House, "Modern Synthetic Reactions," 2nd Ed., W. A. Benjamin,FNC., Menlo Park, 1972, pp. 334-335 and references cited within.

8. B. M. Trost and T. H. Salzmann, J. Am. Chem. Soc., 95, 6840 (1973).This procedure can be utilized for the synthesis of α,β-unsaturatedlactams, sulfones and sultams. Literature procedures for the formationof α-anions of the above active methylene compounds are incorporated intable 2 where pertinent.

9. C. V. Wilson and J. F. Stenberg,

Org. Syn., Coll. Vol. 4, 564 (1963).

10. T. Satoh, S. Suzuki, Y. Suzuki, Y. Miyaji and Z. Imai, Tet. Lett.,(52) 4555 (1969).

11. A. C. Cope and E. Ciganek, Org. Syn., Coll. Vol. 4, 339 (1963).

12. S. L. Friess, J. Am. Chem. Soc., 71, 2571 (1949).

13. S. L. Friess and P. E. Frankenburg, Ibid., 74, 2679 (1952).

14. C. H. Hassall, Org. Reactions, 9, 73 (1957).

15. Borsche, Ber., 48, 682 (1915).

16. Ibid., 56, 2012, 2132 (1923).

17. Ibid., 59, 237 (1926).

18. Cawley and Plant, J. Chem. Soc., 1214 (1938).

19. Attenburrow, et. al., Ibid., 571 (1945).

20. E. Winterfeldt, Ber Deutsch Chem Ges., 97, 2463 (1964).

21. J. Hebky and J. Kejha, CA, 50, 155326.

22. J. V. Greenhill, Chem. Soc. Rev., 6, 277 (1977).

23. J. A. Leben, Ber., 29, 1673, (1896).

24. Von Pechmann and W. Welsh, Ber., 17, 2391 (1884).

25. J. H. Boyer and W. Schoen, Org. Syntheses, Coll. Vol. IV, 532(1963).

26. H. Hiari and K. Miyata, J. Patent 72, 42,832, Jan. 28, 1970.

27. D. E. Heitmeier, J. T. Hortenstine Jr., and A. P. Gray, J. Org.Chem., 36, 1449 (1971).

28. T. S. Hamilton and R. J. Adams, J. Am. Chem. Soc., 50, 2260 (1928).

29. J. L. Herrmann and R. H. Schlessinger, J. Am. Chem. Soc., Chem.Comm., 711 (1973).

30. G. H. Posner and G. L. Lomis, Chem. Comm., 892 (1972).

31. K. Iwai, Chem. Lett., 385 (1974).

32. P. Hullot et. al., Can. J. Chem., 54, 1098 (1976).

33. P. A. Zoretic and F. Barcelos, Tet. Lett., 529 (1977).

34. B. M. Trost and R. A. Kunz. J. Org. Chem., 34 (1974).

35. J. P. Depres, A. E. Greene and P. Crabbe, Tet. Lett., 2191 (1978).

36. J. K. Crandall and A. C. Clark, Tet. Lett., 325-28 (1969).

37. J. B. Bush and H. Finkbiener, J. Am. Chem. Soc., 90, 5903 (1968).

38. H. O. House, "Modern Synthetic Reactions," 2nd Ed., W. A. Benjamin,Inc., Menlo Park, 1972, pp. 492-628 and references cited within.

39. N. C. Corbin, P. Fraher, and J. D. McChesney, J. Pharm. Science, 68,1501 (1979).

40. Gor, Harmon, Levisalles and Wagnon, Chem. Comm., 88 (1973).

41. G. H. Posner, Org. Reactions, 19, 1 (1972).

42. H. O. House, Acc. Chem. Res., 9 (1976).

43. Truce, Hollister, Lindy and Parr, J. Org. Chem., 33, 43 (1968).

44. Truce and Vrencur, J. Org. Chem., 35, 1226 (1970).

45. M. Julia and Arnould, Bull. Soc. Chim. Fr., 743, 746 (1973).

46. A. D. Bliss, W. K. Cline, C. E. H. Milton and O. J. Sweeting, J.Org. Chem., 28, 3537 (1963).

47. H. D. Hartough, "Chemistry of Heterocyclic Compounds," 3,Interscience Publishers, Inc., New York (1952).

48. A. Williams, "Furans Synthesis and Applications," Noyes Data Corp.,New Jersey, 1973.

49. M. E. Garst, J. N. Bonfiglio, D. A. Grudoski, and J. Marks, Tet.Lett., 2671 (1978).

50. Wolf and Folkers, Org. Reactions, 6, 443-468 (1951).

51. G. Stork and L. Maldonado, J. Am. Chem. Soc., 73, 5286 (1971).

52. G. Stork and L. Maldonado, Ibid., 76, 5272 (1974).

53. R. Woodward and Eastman, J. Am. Chem. Soc., 68, 2229 (1946).

54. R. Woodward and Eastman, Ibid., 66, 849 (1944).

55. V. Luhmann and W. Luttke, Chem. Ber., 105, 1350 (1972).

56. I. J. Borowitz and G. J. Williams, J. Org. Chem., 32, 4157 (1967).

57. J. March, "Advanced Organic Chemistry," 2nd Ed., McGraw HIll BookCompany, New York, 1977, pp. 363-365.

58. R. Gorski, G. J. Wolber and J. Wemple, Tet. Lett., 2577 (1976).

59. T. A. Morgan and B. Ganem, Tet. Lett., 2773 (1980).

60. M. Koreeda and H. Akagi, Tet. Lett., 1197 (1980).

61. N. Sugiyama, M. Yamamoto and C. Kashima, Bull. Chem. Soc. Japan, 42,1357 (1969).

62. G. M. Bennett and L. V. D. Scorah, J. Chem. Soc., 194 (1927).

63. A. Belanger and P. Brassard, Chem. Comm., 863 (1972).

64. J. Fried, "Heterocyclic Compounds," ed. by R. C. Elderfield, Wiley,New York, 1950, Vol. 1, pp. 358-370.

65. L. F. Cavalieri, Chem. Rev., 41, (525) (1947).

66. E. Tihanyi, M. Gai, and P. Dvortsak, Heterocycles, 20, 571 (1983).

67. Y. Kurasawa, M. Ichikawa, A. Sakukura and H. Takada, Chem. Pharm.Bull., Tokyo, 32, 4140 (1984).

68. Ibid., 30, 336 (1982).

69. K. Takacs and K. Harsanyi, Chem. Ber., 103, 2330 (1970).

70. P. W. Searle and W. K. Warburton, J. Chem. Soc., Perkins Trans., 1,85 (1974).

71. A. R. Katritzky, B. Wallis, R. T. C. Brownlee, and R. D. Topsom,Tet., 21, 1681 (1965).

72. S. Kubota and M. Uda, Chem. Pharm. Bull., 21, 1342, (1973).

73. S. Kubuta and M. Uda, Ibid., 24, 1336 (1976).

74. R. K. Howe, T. A. Gruner, L. G. Carter, L. L. Black, and J. E.Franz, J. Org. Chem. 43, 3736 (1978).

75. R. Boyle, F. Eloy and R. Lenaers, Helv. Chim. Acta., XLVI, 1073(1973).

76. J. Sauer and K. K. Mayer, Tet. Lett., 319 (1968).

77. G. Beck, Chem. Ber., 84, 688 (1951).

78. J. Goerdeler and R. Sappelt, Chem. Ber., 100, 2064 (1967).

79. T. J. Giacobbe, J. Het. Chem. 15, 1227 (1978).

80. Kurt Pilgram, Ibid., 19, 823 (1982).

81. M. Kishi, H. Ishitobi, W. Nagata, and T. Tsuji, Heterocycles, 13 197(1979).

82. A. K. Saund and M. K. Mathur, Int. J. Peptide Protein Res., 5, 7,(1964).

83. Y. Fuju Moto et. al., Heterocycles, 6, 1604 (1977).

84. For a discussion of the optimal conditions required for selectivelygenerating thermodynamic or kinetic enolates, see J. C. Stowell,"Carbanions in Organic Synthesis," John Wiley and Sons, Inc., New York,1979, pp. 8-11 and references cited therein.

What is claimed is:
 1. A compound which is ##STR60## W is O or S; R is Hor CH₃ ;E₁ is O, S, CO, SO₂ or a single bond. X_(a) is CH₂, CH(CH₃), CH₂CH₂, CH₂ CH₂ CH₂ or CO; E is a single bond, CH₂ or O; Q is selected from##STR61## wherein Q-1 through Q-87 may be optionally substituted with 1or 2 groups selected from C₁ -C₂ alkyl or C₁ -C₂ haloalkyl; R₅ and R₆are independently H or C₁ -C₃ alkyl; X_(b) is O or NR₅ ; and X_(c) is O,S, SO, SO₂ or NR₅ ; R₁ is H, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, halogen,nitro, C₁ -C₃ alkoxy, SO₂ NR_(a) R_(b), C₁ -C₃ alkylthio, C₁ -C₃alkylsulfinyl, C₁ -C₃ alkylsulfonyl, CH₂ CN, CN, CO₂ R_(c), C₁ -C₃haloalkoxy, C₁ -C₃ haloalkylthio, C₂ -C₄ alkoxyalkyl, C₂ -C₄alkylthioalkyl, CH₂ N₃ or NR_(d) R_(e) ; R_(a) is H, C₁ -C₄ alkyl, C₂-C₃ cyanoalkyl, methoxy or ethoxy; R_(b) is H, C₁ -C₄ alkyl or C₃ -C₄alkenyl; or R_(a) and R_(b) may be taken together as --(CH₂)₃ --,--(CH₂)₄ --, --(CH₂)₅ -- or --CH₂ CH₂ OCH₂ CH₂ --; R_(c) is C₁ -C₄alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₂ -C₄ haloalkyl, C₂ -C₃cyanoalkyl, C₅ -C₆ cycloalkyl, C₄ -C₇ cycloalkylalkyl or C₂ -C₄alkoxyalkyl; R_(d) and R_(e) are independently H or C₁ -C₂ alkyl;##STR62## X is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄haloalkyl, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, halogen, C₂ -C₅alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃alkyl)amino or C₃ -C₅ cycloalkyl; Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy,C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, C₂ -C₅alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃alkyl)amino, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy, C₂ -C₅alkylthioalkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkynyl, azido, cyano, C₂ -C₅alkylsulfinylalkyl, C₂ -C₅ alkylsulfonylalkyl, ##STR63## m is 2 or 3; L₁and L₂ are independently O or S; R₂ is H or C₁ -C₃ alkyl; R₃ and R₄ areindependently C₁ -C₃ alkyl; Z is CH, CCH₃, CC₂ H₅, CCl or CBr;and theiragriculturally suitable salts; provided that (a) when X is Cl, F, Br orI, then Z is CH and Y is OCH₃, OC₂ H₅ N(OCH₃)CH₃, NHCH₃, N(CH₃)₂ or OCF₂H; (b) when X or Y is C₁ haloalkoxy, then Z is CH; (c) when J is J-2 orJ-3, the substituent E₁ X_(a) Q and the sulfonylurea bridge are onadjacent carbon atoms; (d) when E is O, then J is J-1 and W is O; (e)when W is S, then R is H, Z is CH and Y is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃,C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, CH(OCH₃)₂or 1,3-dioxolan-2-yl; (f) when the total number of carbon atoms of X andY is greater than four, then the number of carbons of R₁ must be lessthan or equal to two, and the number of carbons of the substituent on Qmust also be less than or equal to two; (g) when J is J-1 wherein E is asingle bond, X_(a) is CH₂, CH(CH₃) or CH₂ CH₂ and Q is a 5-memberedheterocyclic ring containing one endocyclic double bond or a 6-memberedheterocyclic ring containing 1 or 2 endocyclic double bonds which isunsubstituted or substituted by one or more C₁ -C₄ alkyl groups thensaid heterocycle must contain at least one nitrogen and be bound toX_(a) through nitrogen; and (h) when X_(a) is CO then E₁ is a singlebond.
 2. The compound of Formula I of claim 1 whereinE₁ is a singlebond; X_(a) is CH₂, CH(CH₃), CH₂ CH₂ or CH₂ CH₂ CH₂ ; and R₁ is H, C₁-C₃ alkyl, C₁ -C₃ haloalkyl, halogen, nitro, C₁ -C₃ alkoxy, SO₂ NR_(a)R_(b), C₁ -C₃ alkylthio, C₁ -C₃ alkylsulfinyl, C₁ -C₃ alkylsulfonyl, CH₂CN, CN, CO₂ R_(c), C₁ -C₃ haloalkoxy or C₁ -C₃ haloalkylthio.
 3. Thecompounds of Formula I of claim 1 wherein E is a single bond and Z isCH.
 4. The compounds of Formula I of claim 1 where E is CH₂, W is 0, Zis CH and E₁ is a single bond.
 5. The compounds of Formula I of claimwhere E is 0, Z is CH and E₁ is a single bond.
 6. The compounds of claim3 whereinW is 0; E₁ is a single bond; X_(a) is CH₂ or CH₂ CH₂ ; R is H;W is 0; R₁ is H, F, Cl, Br, C₁ -C₂ alkyl, C₁ -C₃ alkoxy, C₁ -C₃alkylthio, or C₁ -C₂ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthiosubstituted with 1-3 atoms of F, Cl or Br; X is C₁ -C₂ alkyl, C₁ -C₂alkoxy, Cl, F, Br, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂CF₃, CH₂ Cl or CH₂ Br; and Y is H, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, CH₂OCH₃, CH₂ OCH₂ CH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂,OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, CH₂ SCH₃, ##STR64## OCF₂ H, SCF₂ H,cyclopropyl, C.tbd.CH or C.tbd.CCH₃.
 7. The compounds of claim 6 whereinJ is J-1.
 8. The compound of claim 1 which isN-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-oxo-1-pyrrolidinylmethyl)benzenesulfonamide.9. The compound of claim 1 which isN-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-oxo-3-oxazolidinylmethyl)-3-thiophenesulfonamide.10. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 1and at least one of the following: surfactant, solid or liquid diluent.11. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 2and at least one of the following: surfactant, solid or liquid diluent.12. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 3and at least one of the following: surfactant, solid or liquid diluent.13. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 4and at least one of the following: surfactant, solid or liquid diluent.14. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 5and at least one of the following: surfactant, solid or liquid diluent.15. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 6and at least one of the following: surfactant, solid or liquid diluent.16. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 9and at least one of the following: surfactant, solid or liquid diluent.17. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 8and at least one of the following: surfactant, solid or liquid diluent.18. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 9and at least one of the following: surfactant, solid or liquid diluent.19. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 1. 20. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 2. 21. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim3.
 22. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 4. 23. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 5. 24. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim6.
 25. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 7. 26. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 8. 27. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of the compound ofclaim 9.